My First Five Years as a CEO: My Biggest Lessons Learned
A few years ago, the Making Waves community came together to define our core values, and one of my favorites is Learn & Grow: We stretch ourselves by staying curious and testing new ideas. We reflect, celebrate, iterate, and share our learning to support others’ growth.
This summer marks an important personal and professional milestone for me: my 5th anniversary as CEO of Making Waves Education Foundation. It’s been fun to look back on my journey in education and reflect on the lessons I’ve learned and how I’ve grown, especially during my first five years as CEO.
After starting my career as a teacher, I spent 10 years leading teams at Teach For America. I learned how to be a manager, to lead with an equity lens as a white male, to shape team culture, and to define and drive strategy. When I joined Making Waves five years ago, I was excited to put into action all my leadership learnings as the organization’s first-ever CEO.
Five years into my role, I am “learning out loud” to share some of the lessons that have helped me get better, be more effective, and sustain my energy and commitment to the work. My hope is that sharing some of my biggest leadership lessons can support the learning and growth of other nonprofit leaders.
My experience is just one experience – it’s unique to me and these lessons are not a solution to challenges faced by nonprofit leaders. For aspiring leaders and others in executive leadership, I do hope though that you can find something here that resonates with your own experiences or provides a fresh perspective that helps you lead and sustain your leadership in the nonprofit sector.
How to define an approach to strong, inclusive decision-making
Decision-making is an Achilles heel and pain point for so many organizations. I often talk to friends at other organizations who a) complain about the way “leadership” makes decisions or b) complain about how teams respond to leaders’ decisions. It sometimes feels like a universal truth that organizations will have a leadership vs. team divide.
This was definitely a pain point for us at Making Waves too, though I don’t think it has to be this way. After lots of bumps in the road on this front, we felt ready to tackle this challenge last year, and we’re now doing a few things that have put us on a batter path. Decision-making is imperfect, but that shouldn’t stop leaders from working on ways to be more inclusive and trying new ways of operating even if it feels hard.
Here are some key learnings:
1. Define your decision-making process
I’m inspired by Maurice Mitchell’s piece, Building Resilient Organizations. He names this leadership vs. team challenge for organizations and lays out solutions:
- First, be clear about an organization’s governance structure and why this structure enables its mission.
- Then be transparent about why certain leadership structures exist.
- Lastly, define how decisions are made.
Our senior leadership team followed this guidance and spent time defining this for Making Waves. We then shared it with our team, codifying it in a memo and discussing it together at an All-Hands meeting.
2. Distribute decision-making power
Consider: when is it most efficient or effective for decisions to be made by you, by your senior leadership team, or by other people?
We got clear that some decisions will be made by our senior leadership team and informed by stakeholder input; we called these “Big Bet Decisions” because of their significant org-wide impact and used a version of the RAPID decision-making framework to guide our approach.
We also got clear that most decisions should be made by other team members throughout the organization since better decisions can be made when those closer to the work have the autonomy to make those calls. This is the work we’re focused on now – creating norms and guidance so that throughout the layers we have clarity on decision-makers and how decisions get made.
3. Communicate consistently with your board
Parter with your board so they can help you achieve your goals. During my first few years as CEO, I realized I wasn’t communicating early enough about decisions or priorities, and it was causing confusion and slowing us all down.
I’m so lucky to have a board that is all-in on our mission, supports my leadership, and wants us to thrive. So, I shifted to consistently partner and communicate with the board to position them to help guide, strengthen, and champion decisions early in the process.
Here’s what worked:
- Bring board members into ideas and challenges early so they can help you land solutions. Have a deep dive topic each board meeting to provide context for a challenge and ways to engage around solutions.
- Build individual relationships between board meetings and leverage members of board committees to be ambassadors to the full board.
- Send a monthly email to the board that shares organizational updates at a super high level, so they have a consistent view into our priorities, progress, wins, and challenges.
